Table 1. Ligand Screening for Nickel-Catalyzed C–N Bond Cyanation^a.

entry	ligand (mol %)	yield (%)	rr (2a:3a:4a)
1	dppb	49	18:29:53
2	L1	87	68:10:22
3	L2	trace	trace
4	L3	80	84:5:11
5	L4	66	60:16:24
6	L5	22	76:16:8
7	L6	26	72:15:13
8	L7	35	86:6:8

^aReaction conditions: benzyl ammonium salts 1a (0.15 mmol, 1.0 equiv), NiBr₂·(diglyme) (12 mol %), ligand (15 mol %), CO₂/NH₃ (15/15 mL), Zn (1.2 equiv), PhSiH₃ (5.0 equiv), and ZnF₂ (50 mol %) were stirred in NMP:diglyme (0.5:0.1 mL) at 120 °C for 28 h. Yields and regioselectivities were determined by GC. dppb = 1,4-bis(diphenylphosphino)butane.